- Shape-persistant macrocycles with terpyridine units: Synthesis, characterization, and structure in the crystal
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The synthesis of a variety of shape-persistent macrocycles with either one (1a-d, 2) or two (opposing) terpyridine units (3, 4, 5a-c) and inner diameters of up to 2 nm is described. The sequences are mainly based on transition metal cross-coupling reactio
- Grave, Christian,Lentz, Dieter,Schaefer, Andreas,Samori, Paolo,Rabe, Juergen P.,Franke, Peter,Schlueter, A. Dieter
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p. 6907 - 6918
(2007/10/03)
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- Solid-phase synthesis of phenylacetylene oligomers utilizing a novel 3-propyl-3-(benzyl-supported) triazene linkage
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Sequence-specific phenylacetylene oligomers consisting of functionalized monomers (hexyl benzoate, hexyl phenyl ether, benzonitrile, and tert-butylphenyl) are synthesized in gram quantities using solid-phase methods. Growing oligomers are attached to a divinylbenzene cross-linked polystyrene support by the 1-aryl-3-propyl-3-(benzyl-supported) triazene moiety. This linkage is obtained by reaction of arenediazonium tetrafluoroborate salts with a n-propylamino-modified Merrifield resin. Condensation strategies are described, producing oligomers with higher yields and simplified procedures compared to solution-phase methods. Terminal acetylene is protected with a trimethylsilyl group. After deprotection of the resin-bound terminal acetylene, an aryl iodide monomer or an aryl iodide-terminated oligomer is coupled to the supported oligomer using a palladium(O) catalyst. The cycle can be repeated to produce sequence-specific oligomers of varying length and functionality. The resulting oligomers are liberated from the polymer support by cleavage of the 1-aryl-3-propyl-3-(benzyl-supported) triazene group by reaction with iodomethane producing an aryl iodide.
- Nelson, James C.,Young, James K.,Moore, Jeffrey S.
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p. 8160 - 8168
(2007/10/03)
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